5β,19-Epoxycucurbitane triterpenoids from momordica charantia and their anti-inflammatory and cytotoxic activity

Chia Ching Liaw; Hui Chi Huang; Ping Chun Hsiao; Li Jie Zhang; Zhi Hu Lin; Syh Yuan Hwang; Feng Lin Hsu; Yao Haur Kuo

doi:10.1055/s-0034-1383307

5β,19-Epoxycucurbitane triterpenoids from momordica charantia and their anti-inflammatory and cytotoxic activity

Chia Ching Liaw, Hui Chi Huang, Ping Chun Hsiao, Li Jie Zhang, Zhi Hu Lin, Syh Yuan Hwang, Feng Lin Hsu, Yao Haur Kuo

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

Five new 5β,19-epoxycucurbitane triterpenoids, taikugausins A-E (1 -5), together with 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (6), have been isolated and characterized from the 70% EtOH extract of the fresh fruits of Momordica charantia. The chemical structures of compounds 1-6 were elucidated on the basis of extensive spectroscopic analyses, especially 2D NMR (HMQC, HMBC, and NOESY) experiments and HRESIMS data. The relationship between NMR chemical shifts and the configuration of C-19 with an OMe group in 5β,19-epoxycucurbitane are described. Among them, compounds 3 and 4 exhibited remarkable anti-inflammatory activities by the inhibition of nitric oxide production at the concentration of 10 μg/mL. In addition, 3 and 4 also showed moderate cytotoxicity against WiDr, Hep G2, MCF-7, and HEp-2 human tumor cell lines.

Original language	English
Pages (from-to)	62-70
Number of pages	9
Journal	Planta Medica
Volume	81
Issue number	1
DOIs	https://doi.org/10.1055/s-0034-1383307
Publication status	Published - Dec 3 2015

Keywords

5β,19-epoxycucurbitane
Anti-inflammatory activity
Cucurbitaceae
Cytotoxicity
Momordica charantia
Taikuguasins

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1055/s-0034-1383307

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title = "5β,19-Epoxycucurbitane triterpenoids from momordica charantia and their anti-inflammatory and cytotoxic activity",

abstract = "Five new 5β,19-epoxycucurbitane triterpenoids, taikugausins A-E (1 -5), together with 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (6), have been isolated and characterized from the 70% EtOH extract of the fresh fruits of Momordica charantia. The chemical structures of compounds 1-6 were elucidated on the basis of extensive spectroscopic analyses, especially 2D NMR (HMQC, HMBC, and NOESY) experiments and HRESIMS data. The relationship between NMR chemical shifts and the configuration of C-19 with an OMe group in 5β,19-epoxycucurbitane are described. Among them, compounds 3 and 4 exhibited remarkable anti-inflammatory activities by the inhibition of nitric oxide production at the concentration of 10 μg/mL. In addition, 3 and 4 also showed moderate cytotoxicity against WiDr, Hep G2, MCF-7, and HEp-2 human tumor cell lines.",

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AU - Liaw, Chia Ching

AU - Huang, Hui Chi

AU - Hsiao, Ping Chun

AU - Zhang, Li Jie

AU - Lin, Zhi Hu

AU - Hwang, Syh Yuan

AU - Hsu, Feng Lin

AU - Kuo, Yao Haur

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N2 - Five new 5β,19-epoxycucurbitane triterpenoids, taikugausins A-E (1 -5), together with 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (6), have been isolated and characterized from the 70% EtOH extract of the fresh fruits of Momordica charantia. The chemical structures of compounds 1-6 were elucidated on the basis of extensive spectroscopic analyses, especially 2D NMR (HMQC, HMBC, and NOESY) experiments and HRESIMS data. The relationship between NMR chemical shifts and the configuration of C-19 with an OMe group in 5β,19-epoxycucurbitane are described. Among them, compounds 3 and 4 exhibited remarkable anti-inflammatory activities by the inhibition of nitric oxide production at the concentration of 10 μg/mL. In addition, 3 and 4 also showed moderate cytotoxicity against WiDr, Hep G2, MCF-7, and HEp-2 human tumor cell lines.

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5β,19-Epoxycucurbitane triterpenoids from momordica charantia and their anti-inflammatory and cytotoxic activity

Abstract

Keywords

ASJC Scopus subject areas

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